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[ CAS No. 915403-16-6 ] {[proInfo.proName]}

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Chemical Structure| 915403-16-6
Chemical Structure| 915403-16-6
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Product Details of [ 915403-16-6 ]

CAS No. :915403-16-6 MDL No. :MFCD20668938
Formula : C10H11N3O Boiling Point : -
Linear Structure Formula :- InChI Key :CWKOUGPJRVVYQX-UHFFFAOYSA-N
M.W : 189.21 Pubchem ID :59198499
Synonyms :

Safety of [ 915403-16-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 915403-16-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 915403-16-6 ]

[ 915403-16-6 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 958230-19-8 ]
  • [ 924655-39-0 ]
  • [ 75-04-7 ]
  • [ 915403-16-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde; 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde; ethylamine In 2-methoxy-ethanol; water at 120℃; Stage #2: With hydrogenchloride; water at 50℃; for 1.5h; Stage #3: With sodium hydrogencarbonate In water 1.3 3. 4-Ethylamino-lH-pyrrolo[2,3-b]pyridine-5-carbaldehyde; [0083] A mixture of 4-chloro-lH-pyrrolo[2,3-Z?]ρyridine-5-carbaldehyde and 4- chloro-l-triisopropylsilanyl-lH-pyrrolo[2,3-]pyridine-5-carbaldehyde (1.016 g, from above step), ethyl amine (70 wt. % solution in water, 8mL, 100 mmol) in methoxy-ethanol (4 mL) is heated at 1200C in a sealed tube. After overnight, the reaction mixture is cooled to room temperature and concentrated. The residue is dissolved in HCl solution (IN, 20 mL) and heated at 5O0C. After stirring for 1.5 hours, the reaction mixture is basifed with saturated sodium bicarbonate solution to a pΗ of 8. The solid is collected by filtration and washed with water, hexanes, and dried to afford the title compound as a solid: 1H NMR 600 MHz (DMSO-J6) δ 11.82 (s, IH), 9.75 (s, IH), 9.30 (t, 1 H, J= 4.8 Hz), 8.19 (s, 1 H), 7.19 (/,1 H, J= 3.6 Hz), 6.72 (m, IH), 3.73-3.69 (m, 2H), 1.30 (t, 3H, J= 7.2 Hz); MS m/z 190.2 (M + I)-
  • 2
  • [ 915403-19-9 ]
  • [ 915403-16-6 ]
  • 3-[(4-ethylamino-1H-pyrrolo[2,3-b]pyridine-5-ylmethylene)-amino]-5-methoxy-benzoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In toluene for 24h; Heating / reflux; 1.4 4. 3-[(4-Ethylamino-lH-pyrrolo[2,3-]ρyridine-5-ylmethylene)-amino]-5- methoxy-benzoic acid ethyl ester; EPO [0085] A mixture of 4-ethylamino-lH-pyrrolo[2,3-]pyridme-5-carbaldehyde(918 mg, 4.85 mmol), 3-amino-5-methoxyl-benzoic acid ethyl ester (1.14g, 5.84 mmol), andp- toluenesulfonic acid monohydrate (92 mg, 0.48mmol) in toluene (100 ml) is heated at reflux with azotropic removal of water. After 24 hours, the reaction mixture is cooled to room temperature and concentrated. The residue is triturated in methanol (20 mL) and water (100 mL). The solid is collected by filtration, washed with water, and dried to afford the title compound as a solid: 1H NMR 400 MHz (DMSO-^) δ 11.62 (s, IH), 10.27 (t, IH, J= 5.4 Hz), 8.80 (s, 1 H), 8.16 (s, 1 H), 7.40 (s,l H), 7.29 (s, IH), 7.16 (m, IH), 7.13 (m, IH), 6.73 (m, IH), 4.35 (g, 2H, J= 6.8 Hz), 3.86 (s, 3H), 3.86-3.78 (m, 2H), 1.39 - 1.32 (m, 6H); MS m/z 367.1 (M + 1).
  • 3
  • [ 924655-39-0 ]
  • [ 75-04-7 ]
  • [ 915403-16-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde; ethylamine In 2-methoxy-ethanol; water at 120℃; Stage #2: With hydrogenchloride; water at 50℃; for 1.5h; Stage #3: With sodium hydrogencarbonate In water 1.3 3. 4-Ethylamino-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde A mixture of 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1 g, 2.97 mmol), ethyl amine (70 wt. % solution in water, 8 mL, 100 mmol) in methoxyethanol (4 mL) is heated at 120° C. in a sealed tube. After overnight, the reaction mixture is cooled to room temperature and concentrated. The residue is dissolved in HCl solution (1N, 20 mL) and heated at 50° C. After stirring for 1.5 hours, the reaction mixture is basified with saturated sodium bicarbonate solution to pH=8. The solid is collected by filtration and washed with water, then hexanes, dried to afford the title compound as a solid. 1H NMR 600 MHz (DMSO-d6) δ 11.82 (s, 1H), 9.75 (s, 1H), 9.30 (t, 1H, J=4.8 Hz), 8.19 (s, 1H), 7.19 (t, 1H, J=3.6 Hz), 6.72 (m, 1H), 3.73-3.69 (m, 2H), 1.30 (t, 3H, J=7.2 Hz); MS m/z 190.2 (M+1).
  • 4
  • [ 915403-16-6 ]
  • [ 958230-33-6 ]
  • [ 958230-20-1 ]
YieldReaction ConditionsOperation in experiment
With piperidine In ethanol at 20 - 120℃; 1.4 4. 3-(9-Ethyl-8-imino-8,9-dihydro-3H-3,4,9-triaza-cyclopenta[a]naphthalen-7-yl)-5-methoxy-benzoic acid ethyl ester 4-Ethylamino-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1 g, 5.3 mmol) and 3-cyanomethyl-5-methoxy-benzoic acid ethyl ester (1.3 g, 5.8 mmol) are dissolved in ethanol (4 mL) and piperidine (2 mL, 21.2 mmol) is added at room temperature. The reaction mixture is heated at 120° C. and stirred for 24 h. The reaction mixture is then concentrated and dried to yield the crude product. The crude product is used for the next step without any further purification. MS m/z 391.1 (M+1).
  • 5
  • [ 958230-19-8 ]
  • [ 75-04-7 ]
  • [ 915403-16-6 ]
YieldReaction ConditionsOperation in experiment
92% In 2-methoxy-ethanol; water at 130℃; 49.1 Step 1: 4-(ethylamino)-JH-pyrrolo[2, 3-bJpyridine-5-carbaldehyde Example 49 3-(2,6-Difluoro-3,5-dimethoxyphenyl)-1-ethyl-3,4,7,9-tetrahydro-1H- pyrrolo j3’,2’:5,6j pyrido j4,3-dj pyrimidine-2,8-dione Step 1: 4-(ethylamino)-JH-pyrrolo[2, 3-bJpyridine-5-carbaldehyde A mixture of 4-chloro- 1 H-pyrrolo[2,3 -b]pyridine-5 -carbaldehyde (CAS 958230-19-8, Lakestar Tech, Lot: 124-132-29: 3.0 g, 17 mmol) and ethylamine (1OM in water, 8.3 mL,83 mmol) in 2-methoxyethanol (20 mL, 200 mmol) was heated to 130 °C and stirredovernight. The mixture was cooled to room temperature then concentrated under reducedpressure. The residue was treated with iN HC1 (30 mL) and stirred at room temperature for 1h then neutralized with saturated NaHCO3 aqueous solution. The precipitate was collected viafiltration then washed with water and dried to provide the desired product (2.9 g, 92 %). LCMS calculated for C10H12N30 [M+H] mlz: 190.1; found: 190.1.
92% In 2-methoxy-ethanol; water at 130℃; 1.1 Step 1:
4-(ethylamino)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (CAS No.958230-19-8, Lakestar Tech, Lot: 124-132-29: 3.0 g, 17 mmol) and ethylamine (10M in water, 8.3 mL, 83 mmol) in 2-methoxyethanol (20 mL, 200 mmol) was heated to 130° C. and stirred overnight. The mixture was cooled to room temperature then concentrated under reduced pressure. The residue was treated with 1N HCl (30 mL) and stirred at room temperature for 1 h then neutralized with saturated NaHCO3 aqueous solution. The precipitate was collected via filtration then washed with water and dried to provide the desired product (2.9 g, 92%). LC-MS calculated for C10H12N3O [M+H]+ m/z: 190.1; found: 190.1.
92% In 2-methoxy-ethanol; water at 130℃; Inert atmosphere;
92% In 2-methoxy-ethanol; water at 130℃; 5.1 Step 1:
4-(ethylamino)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (CAS No.958230-19-8, Lakestar Tech, Lot: 124-132-29: 3.0 g, 17 mmol) and ethylamine (10M in water, 8.3 mL, 83 mmol) in 2-methoxyethanol (20 mL, 200 mmol) was heated to 130° C. and stirred overnight. The mixture was cooled to room temperature then concentrated under reduced pressure. The residue was treated with 1N HCl (30 mL) and stirred at room temperature for 1 h then neutralized with saturated NaHCO3 aqueous solution. The precipitate was collected via filtration then washed with water and dried to provide the desired product (2.9 g, 92%). LC-MS calculated for C10H12N3O [M+H]+ m/z: 190.1; found: 190.1.

  • 6
  • [ 651734-54-2 ]
  • [ 915403-16-6 ]
  • [ 1513859-26-1 ]
YieldReaction ConditionsOperation in experiment
82% Step 2: 5-[(2, 6-dUluoro-3, 5-dimethoxyphenyaminoJmethyl}-N-ethyl-1H-pyrrolo[2, 3- bJpyridin-4-amine A mixture of 4-(ethylamino)- 1 H-pyrrolo[2,3 -b]pyridine-5 -carbaldehyde (7.0 g, 37 mmol), 2,6-difluoro-3 ,5 -dimethoxyaniline (9.1 g, 48 mmol) and [(1 S)-7,7-dimethyl-2-oxobicyclo[2.2. 1 ]hept- 1 -yl]methanesulfonic acid (Aldrich, cat 21360: 2 g, 7 mmol) inxylenes (250 mL) was heated to reflux with azeotropic removal of water using Dean-Stark for2 days at which time LC-MS showed the reaction was complete. The mixture was cooled toroom temperature and the solvent was removed under reduced pressure. The residue was dissolved in tetrahydrofuran (500 mL) and then 2.0 M lithium tetrahydroaluminate in THF (37 mL, 74 mmol) was added slowly and the resulting mixture was stirred at 50 C for 3 h then cooled to room temperature. The reaction was quenched by addition of water, 15% aqueous NaOH and water. The mixture was filtered and washed with THF. The filtrate wasconcentrated and the residue was washed with CH2C12 and then filtered to get the pure product (ii g, 82%). LC-MS calculated for C18H21F2N402 [M+H] mlz: 363.2; found: 363.1.
  • 7
  • [ 915403-16-6 ]
  • [ 1513857-72-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: (1S)-(+)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C
Multi-step reaction with 2 steps 1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 2.2: 0 - 20 °C
Multi-step reaction with 2 steps 1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 20 - 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C
Multi-step reaction with 2 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C

  • 8
  • [ 915403-16-6 ]
  • [ 1513857-77-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: (1S)-(+)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: acetic acid / dichloromethane / 20 °C 5.2: 3 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 50 °C
Multi-step reaction with 6 steps 1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 2.2: 0 - 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: acetic acid / dichloromethane / 20 °C 5.2: 3 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 50 °C
Multi-step reaction with 6 steps 1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 20 - 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 0.5 h / -78 °C 5.1: acetic acid / dichloromethane / 20 °C / Inert atmosphere 5.2: 3 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 50 °C / Inert atmosphere
Multi-step reaction with 6 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: acetic acid / dichloromethane / 20 °C 5.2: 3 h / 20 °C 6.1: sodium hydroxide; water / 1,4-dioxane / 18 h / Heating

  • 9
  • [ 915403-16-6 ]
  • [ 1513858-71-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: (1S)-(+)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 3 h / 20 °C 6.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 20 °C 6.2: 1 h / 20 °C
  • 10
  • [ 915403-16-6 ]
  • [ 1513859-67-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: (1S)-(+)-10-camphorsulfonic acid / toluene / 96 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: triethylamine / tetrahydrofuran / 3 h / 20 °C
  • 11
  • [ 915403-16-6 ]
  • [ 1513860-01-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: (1S)-(+)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C
Multi-step reaction with 3 steps 1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 2.2: 0 - 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C
Multi-step reaction with 3 steps 1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 20 - 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 3.2: 1.5 h / 0 °C
Multi-step reaction with 3 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C

  • 12
  • [ 915403-16-6 ]
  • 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-2-oxo-7-(phenylsulfonyl)-2,3,4,7-tetrahydro-1H-pyrrolo-[3′,2’:5,6]pyrido[4,3-d]pyrimidine-8-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: (1S)-(+)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C
Multi-step reaction with 4 steps 1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 2.2: 0 - 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C
Multi-step reaction with 4 steps 1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 20 - 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 0.5 h / -78 °C
Multi-step reaction with 4 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C

  • 13
  • [ 915403-16-6 ]
  • [ 1513860-02-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: (1S)-(+)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: acetic acid / dichloromethane / 20 °C 5.2: 3 h / 20 °C
Multi-step reaction with 5 steps 1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 2.2: 0 - 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: acetic acid / dichloromethane / 20 °C 5.2: 3 h / 20 °C
Multi-step reaction with 5 steps 1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 20 - 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 0.5 h / -78 °C 5.1: acetic acid / dichloromethane / 20 °C / Inert atmosphere 5.2: 3 h / 20 °C
Multi-step reaction with 5 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: acetic acid / dichloromethane / 20 °C 5.2: 3 h / 20 °C

  • 14
  • [ 915403-16-6 ]
  • [ 1513857-00-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: (1S)-(+)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: pyridinium perbromide hydrobromide / water; isopropyl alcohol / 3 h / 40 °C 3.2: 20 °C
  • 15
  • [ 915403-16-6 ]
  • [ 1513860-41-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: (1S)-(+)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 3 h / 20 °C
  • 16
  • [ 915403-16-6 ]
  • [ 1513857-14-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: (1S)-(+)-10-camphorsulfonic acid / toluene / 96 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: triethylamine / tetrahydrofuran / 3 h / 20 °C 3.1: pyridinium perbromide hydrobromide / water; isopropyl alcohol / 30 °C 3.2: 2 h / 20 °C
  • 17
  • [ 915403-16-6 ]
  • [ 1002719-50-7 ]
  • [ 1513859-66-9 ]
YieldReaction ConditionsOperation in experiment
35% Stage #1: 4-(ethylamino)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde; 2-chloro-6-fluoro-3,5-dimethoxyaniline With (1S)-(+)-10-camphorsulfonic acid In toluene for 96h; Reflux; Dean-Stark; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 50℃; for 3h; 63.4 Step 4: 5-[(2-chloro-6-fluoro-3, 5-dimethoxyp henyl) aminoJmethyl}-N-ethyl-JH-pyrrolo[2, 3- bJpyridin-4-amine Step 4: 5-[(2-chloro-6-fluoro-3, 5-dimethoxyp henyl) aminoJmethyl}-N-ethyl-JH-pyrrolo[2, 3- bJpyridin-4-amine A mixture of 4-(ethylamino)- 1 H-pyrrolo[2,3 -b]pyridine-5 -carbaldehyde (Example 49, Step 1: 1.6 g, 8.3 mmol), 2-chloro-6-fluoro-3,5-dimethoxyaniline (1.7 g, 8.3 mmol) and[(1 S)-7,7-dimethyl-2-oxobicyclo[2.2.1 ]hept- 1 -yl]methanesulfonic acid (Aldrich, cat 21360:0.6 g, 2 mmol) in toluene (200 mL, 2000 mmol) was heated to reflux with azotropic removal of water using a Dean-Stark trap for 4 days. The reaction mixture was cooled to room temperature and concentrated. The residue was dissolved in tetrahydrofuran (40 mL) and then lithium tetrahydroaluminate (0.78 g, 21 mmol) was added dropwise. The mixture was stirredat 50 °C for 3 h then cooled to room temperature. The reaction was quenched by addition of water (0.8 mL), 15 % aqueous NaOH (0.8 mL) then water (2.4 mL). The mixture was filtered and washed with THF. The filtrate was concentrated and the residue was purified by chromatography eluted with 0 to 5 % MeOH in CH2C12 to give the desired product (1.1 g, 35 %). LC-MS calculated for C18H21C1FN402 (M+H) mlz: 379.1; found 379.1.
  • 18
  • [ 915403-16-6 ]
  • 3-(9-ethyl-8-oxo-3,6,8,9-tetrahydro-3,4,7,9-tetraaza-cyclopenta[a]naphthalen-7-yl)-5-methoxy-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / toluene / 24 h / Heating / reflux 2.1: sodium cyanoborohydride / ethanol; N,N-dimethyl-formamide 2.2: 24 h / 20 °C 3.1: triethylamine / tetrahydrofuran / 1 h / 20 °C 3.2: 8 h / 65 °C 3.3: 0.5 h / pH 4 - 5
  • 19
  • [ 915403-16-6 ]
  • N-ethyl-3-(9-ethyl-8-oxo-3,6,8,9-tetrahydro-3,4,7,9-tetraaza-cyclopenta[a]naphthalen-7-yl)-5-methoxy-benzamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / toluene / 24 h / Heating / reflux 2.1: sodium cyanoborohydride / ethanol; N,N-dimethyl-formamide 2.2: 24 h / 20 °C 3.1: triethylamine / tetrahydrofuran / 1 h / 20 °C 3.2: 8 h / 65 °C 3.3: 0.5 h / pH 4 - 5 4.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.2 h / 20 °C 4.2: 2 h / 20 °C
  • 20
  • [ 915403-16-6 ]
  • [ 915403-18-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / toluene / 24 h / Heating / reflux 2.1: sodium cyanoborohydride / ethanol; N,N-dimethyl-formamide 2.2: 24 h / 20 °C
  • 21
  • [ 55052-28-3 ]
  • [ 915403-16-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: -78 - 20 °C 2.1: sec.-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 2.2: 1 h / -78 °C 3.1: 2-methoxy-ethanol; water / 120 °C 3.2: 1.5 h / 50 °C 3.3: pH 8
Multi-step reaction with 3 steps 1.1: sodium hydride; pyridine / mineral oil / 1 h / 0 - 20 °C / Inert atmosphere; Large scale 1.2: 20 h / 20 - 25 °C / Large scale 2.1: sec.-butyllithium / cyclohexane / 0.8 h / -75 - -60 °C / Inert atmosphere; Large scale 2.2: 0.5 h / -75 - -65 °C / Large scale 2.3: 20 - 25 °C / Large scale 3.1: water; 2-methoxy-ethanol / 130 °C
  • 22
  • [ 271-63-6 ]
  • [ 915403-16-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 8 h / 0 - 10 °C / Large scale 2.1: methanesulfonyl chloride / N,N-dimethyl-formamide / 50 - 90 °C / Large scale 3.1: sodium hydride; pyridine / mineral oil / 1 h / 0 - 20 °C / Inert atmosphere; Large scale 3.2: 20 h / 20 - 25 °C / Large scale 4.1: sec.-butyllithium / cyclohexane / 0.8 h / -75 - -60 °C / Inert atmosphere; Large scale 4.2: 0.5 h / -75 - -65 °C / Large scale 4.3: 20 - 25 °C / Large scale 5.1: water; 2-methoxy-ethanol / 130 °C
  • 23
  • [ 55052-24-9 ]
  • [ 915403-16-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: methanesulfonyl chloride / N,N-dimethyl-formamide / 50 - 90 °C / Large scale 2.1: sodium hydride; pyridine / mineral oil / 1 h / 0 - 20 °C / Inert atmosphere; Large scale 2.2: 20 h / 20 - 25 °C / Large scale 3.1: sec.-butyllithium / cyclohexane / 0.8 h / -75 - -60 °C / Inert atmosphere; Large scale 3.2: 0.5 h / -75 - -65 °C / Large scale 3.3: 20 - 25 °C / Large scale 4.1: water; 2-methoxy-ethanol / 130 °C
  • 24
  • [ 651744-48-8 ]
  • [ 915403-16-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sec.-butyllithium / cyclohexane / 0.8 h / -75 - -60 °C / Inert atmosphere; Large scale 1.2: 0.5 h / -75 - -65 °C / Large scale 1.3: 20 - 25 °C / Large scale 2.1: water; 2-methoxy-ethanol / 130 °C
  • 25
  • [ 915403-16-6 ]
  • 3-(2,6-difluoro-3-hydroxy-5-methoxyphenyl)-1-ethyl-8-(morpholinomethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3',2':5,6]pyrido[4,3-d]pyrimidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water / Inert atmosphere; Cooling; Large scale 4.1: lithium diisopropyl amide / tetrahydrofuran / Cooling 4.2: Cooling 5.1: acetic acid / dichloromethane / 4.57 h / 0.27 - 0.32 °C / Inert atmosphere 5.2: 3.17 h / 0.24 - 0.28 °C 6.1: hydrogenchloride / water; 1,4-dioxane / 18 h / 80 °C / Inert atmosphere
  • 26
  • [ 915403-16-6 ]
  • 3-(2,6-difluoro-3,5-bis(methoxy-d3)phenyl)-1-ethyl-8-(morpholinomethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3',2':5,6]pyrido[4,3-d]pyrimidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: acetic acid / dichloromethane / 20 °C 5.2: 3 h / 20 °C 6.1: boron tribromide / dichloromethane / 2.5 h / -78 - 20 °C 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C / Inert atmosphere 7.2: 1 h / 20 °C 8.1: sodium hydroxide; water / 1,4-dioxane / 15 h / 74 °C
  • 27
  • [ 915403-16-6 ]
  • 7-(2,6-difluoro-3,5-dimethoxy-phenyl)-9-ethyl-8-oxo-6,7,8,9-tetrahydro-3,4,7,9-tetraazacyclopenta[a]naphthalene-3-sulfonic acid dimethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water / Inert atmosphere; Cooling; Large scale
  • 28
  • [ 915403-16-6 ]
  • 7-(2,6-difluoro-3,5-dimethoxy-phenyl)-9-ethyl-2-formyl-8-oxo-6,7,8,9-tetrahydro-3,4,7,9-tetraazacyclopenta[a]naphthalene-3-sulfonic acid dimethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water / Inert atmosphere; Cooling; Large scale 4.1: lithium diisopropyl amide / tetrahydrofuran / Cooling 4.2: Cooling
  • 29
  • [ 915403-16-6 ]
  • 7-(2,6-difluoro-3,5-dimethoxy-phenyl)-9-ethyl-2-morpholin-4-ylmethyl-8-oxo-6,7,8,9-tetrahydro-3,4,7,9-tetraaza-cyclopenta[a]naphthalene-3-sulfonic acid dimethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water / Inert atmosphere; Cooling; Large scale 4.1: lithium diisopropyl amide / tetrahydrofuran / Cooling 4.2: Cooling 5.1: acetic acid / dichloromethane / 4.57 h / 0.27 - 0.32 °C / Inert atmosphere 5.2: 3.17 h / 0.24 - 0.28 °C
  • 30
  • [ 915403-16-6 ]
  • 3-(2,6-difluoro-3,5-dihydroxyphenyl)-1-ethyl-8-(morpholinomethyl)-7-(phenylsulfonyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3',2':5,6]pyrido[4,3-d]pyrimidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: acetic acid / dichloromethane / 20 °C 5.2: 3 h / 20 °C 6.1: boron tribromide / dichloromethane / 2.5 h / -78 - 20 °C
  • 31
  • [ 915403-16-6 ]
  • 3-(2,6-difluoro-3,5-bis(methoxy-d3)phenyl)-1-ethyl-8-(morpholinomethyl)-7-(phenylsulfonyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3',2':5,6]pyrido[4,3-d]pyrimidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark 1.2: 3 h / 50 °C 2.1: tetrahydrofuran / 6 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 3.2: 1.5 h / 0 °C 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: acetic acid / dichloromethane / 20 °C 5.2: 3 h / 20 °C 6.1: boron tribromide / dichloromethane / 2.5 h / -78 - 20 °C 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C / Inert atmosphere 7.2: 1 h / 20 °C
Same Skeleton Products
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